CN108676040A - A kind of preparation method and application of 1,2,3- triazoles diphenyl phosphate synanthrin derivative - Google Patents
A kind of preparation method and application of 1,2,3- triazoles diphenyl phosphate synanthrin derivative Download PDFInfo
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- CN108676040A CN108676040A CN201810683260.1A CN201810683260A CN108676040A CN 108676040 A CN108676040 A CN 108676040A CN 201810683260 A CN201810683260 A CN 201810683260A CN 108676040 A CN108676040 A CN 108676040A
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- synanthrin
- diphenyl phosphate
- triazole
- derivatives
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- RDOXTESZEPMUJZ-UHFFFAOYSA-N COc1ccccc1 Chemical compound COc1ccccc1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
Abstract
The present invention relates to food medical treatment cosmetic fields, and in particular to a kind of preparation method and application of 1,2,3 triazole diphenyl phosphate synanthrin derivatives.First using synanthrin as raw material, alkynyl group is introduced using propargyl bromide, azido group is introduced into diphenyl phosphate chloride, diphenylphosphoryl azide is reacted with alkynyl synanthrin by click, by diphenyl phosphate, triazole isoreactivity group is introduced into synanthrin molecule, a kind of 1,2,3 triazole synanthrin derivatives containing diphenyl phosphate are made, and its antioxidant activity is studied, it can be applied to the anti-oxidation field of food medical cosmetic etc..
Description
Technical field
The present invention relates to food medical treatment cosmetic fields, and in particular to one kind 1,2,3- triazole diphenyl phosphate synanthrin spreads out
The preparation method and application of biology, can be used as antioxidant, be applied to the fields such as food medical cosmetic.
Background technology
Synanthrin (Inulin) is also known as inulin.Alantin is a kind of linear direct-connected polysaccharide, by beta-D-fructofuranose and end
End glucose residue is polymerized, widely distributed in nature, is mainly derived from plant.Synanthrin itself has good physics and chemistry
Property has control blood fat, reduces blood glucose, promote enteron aisle mineral absorption, adjust intestinal microflora, it is strong to improve enteron aisle
Health prevents constipation, prevents colon cancer and inhibits the physiological functions such as tumour growth, be widely applied to food, health products, feed,
The numerous areas such as bioenergy and medicine.Polysaccharide, the edible value of synanthrin are eaten as a kind of natural, safe functionality
It is had been to be concerned by more and more people with healthcare function.
The antioxidant activity of polysaccharide is to evaluate one of the important indicator of its health-care effect and medical value, is then had at present
The health products price of anti-aging effects is often higher.Synanthrin derives from a wealth of sources, cheap, is a kind of compatible with good biological
Property natural polysaccharide, however the antioxidant activity of itself is relatively low, based on active principle of stacking, is reacted by click, by phosphoric acid
Diphenyl ester, 1,2,3- triazole isoreactivity group are introduced into synanthrin molecule, and the anti-of synanthrin is significantly improved by chemical modification
Oxidation activity promotes it in the application in the fields such as food medical treatment cosmetics.
Invention content
The present invention provides a kind of preparation method and applications of 1,2,3- triazole diphenyl phosphate synanthrin derivatives, first with
Synanthrin is raw material, prepares alkynyl synanthrin, using sodium azide by diphenyl phosphate chloride Azide, diphenylphosphoryl azide with
Alkynyl synanthrin is reacted by click, and 1,2,3- triazole diphenyl phosphate synanthrin derivatives are made.
Specific technical solution is as follows：
One kind 1,2,3- triazole diphenyl phosphate synanthrin derivatives, described 1,2,3- triazole diphenyl phosphate synanthrin spread out
Biological structure formula is as follows：
The synanthrin derivative molecular amount is 10,000 or so.
The 1,2,3- triazoles diphenyl phosphate synanthrin derivative can be applied to the antioxygen in food medical cosmetic field
In terms of change.
The preparation method of 1,2,3- triazole diphenyl phosphate synanthrin derivative utilizes propargyl bromide using synanthrin as raw material
Alkynyl synanthrin is made, Azide is carried out using sodium azide with diphenyl phosphate chloride, is reacted by click, is made 1,2,3- tri-
Nitrogen azoles diphenyl phosphate synanthrin derivative, includes the following steps：
(1) preparation of alkynyl synanthrin：It takes a certain amount of synanthrin to be scattered in isopropanol to stir evenly, be added a certain amount of
A certain amount of propargyl bromide solution is added dropwise after activating 1h in 5.0%NaOH solution, and 60 DEG C of the reaction was continued 4h, reaction terminates, pours into
In ethanol solution, Precipitation filters, after being washed repeatedly with ethyl alcohol, sample freeze-drying；
(2) preparation of diphenyl phosphate azide：It takes a certain amount of diphenyl phosphate chloride in round-bottomed flask, is added a certain amount of
Sodium azide, a certain amount of acetone soln is then added and makees solvent, reacts at room temperature 5h, vacuum distillation removes solvent；
(3) preparation of 1,2,3- triazoles diphenyl phosphate synanthrin derivative：A certain amount of above-mentioned alkynyl synanthrin is taken to be dissolved in
In a certain amount of DMSO solution, a certain amount of CuI is sequentially added, then institute in a certain amount of (2) is slowly added dropwise in triethylamine solution
The diphenyl phosphate azide solution stated, under nitrogen protection, above-mentioned reaction solution is poured into acetone by 75 DEG C of reaction 48h after reaction
In solution, Precipitation is filtered, is repeatedly washed with acetone, sample dialysis freeze-drying.
Step (1) synanthrin, isopropanol, 5.0%NaOH solution, propargyl bromide dosage are respectively：Per 1.6g synanthrin,
20.0-60.0mL isopropanol, 25.0-50.0mL5.0%NaOH solution, 2.4-6.3mL propargyl bromides.
Step (2) diphenyl phosphate chloride, sodium azide, acetone dosage are respectively：Per 1.5mL diphenyl phosphate chlorides,
1.4-2.7g sodium azide, 25.0-50.0mL acetone.
Step (3) the alkynyl synanthrin, DMSO, CuI, triethylamine, diphenyl phosphate azide solution usage are respectively：Often
2.0g alkynyl synanthrin, 50.0mLDMSO, 0.1-0.2gCuI, 0.5-2.0mL triethylamines, 10.0-15.0g diphenyl phosphate azides
Solution.
Compared with prior art, advantageous effects of the invention are as follows：
1,2,3- triazole as a kind of five-ring heterocycles structure have good bioactivity, such as anti HIV-1 virus, antibacterial,
Anticancer, anti-malarial agents and anti-oxidant etc..In addition, diphenyl phosphate azide has higher reactivity, it is widely applied to antibacterial
In the medicine building-up process such as drug, nonsteroidal anti-inflammatory drug, Claritin, hypertension drug and nerve cell-protective agents.
In the present invention, reacted by click, synthesize with diphenyl phosphate 1,2,3- triazole synanthrin derivatives, and to its into
The test of antioxidant activity is gone, research structure shows that 1,2,3- triazole diphenyl phosphate synanthrin derivatives are significantly anti-oxidant
Activity is substantially better than synanthrin.
Description of the drawings
Fig. 1 is the infrared spectrogram of synanthrin；
Fig. 2 is the infrared spectrogram of alkynyl synanthrin prepared by the embodiment of the present invention 3；
Fig. 3 is the infrared spectrogram of diphenyl phosphate azide prepared by the embodiment of the present invention 3；
Fig. 4 is the infrared spectrogram of 1,2,3- triazole diphenyl phosphate synanthrin derivatives prepared by the embodiment of the present invention 3；
Fig. 5 is that 1,2,3- triazole diphenyl phosphate synanthrin derivatives remove DPPH free radicals in the embodiment of the present invention 3
Ability, CPI 1,2,3- triazole diphenyl phosphate synanthrin derivatives；
Fig. 6 is that 1,2,3- triazole diphenyl phosphate synanthrin derivatives remove hydroxyl radical free radical in the embodiment of the present invention 3
Ability, CPI 1,2,3- triazole diphenyl phosphate synanthrin derivatives；
Fig. 7 is that 1,2,3- triazole diphenyl phosphate synanthrin derivatives remove superoxide anion certainly in the embodiment of the present invention 3
By the ability of base, CPI 1,2,3- triazole diphenyl phosphate synanthrin derivatives.
Specific implementation mode
The present invention is described in detail with reference to the accompanying drawings and examples, but protection scope of the present invention not by attached drawing and
Embodiment is limited.
Embodiment 1：
(1) preparation of alkynyl synanthrin：It takes the synanthrin of 1.6g to be scattered in 20.0mL isopropanols to stir evenly, addition
The propargyl bromide solution of 2.4mL is added dropwise after activating 1h in 25.0mL5.0%NaOH solution, and 60 DEG C of the reaction was continued 4h, reaction terminates,
It pours into ethanol solution, Precipitation, filters, after being washed repeatedly with ethyl alcohol, sample freeze-drying；
(2) preparation of diphenyl phosphate azide：It takes 1.5mL diphenyl phosphate chlorides in round-bottomed flask, 1.4g nitrine is added
Change sodium, the acetone soln of 25.0mL is then added, react at room temperature 5h, vacuum distillation removes solvent；
(3) preparation of 1,2,3- triazoles diphenyl phosphate synanthrin derivative：The above-mentioned alkynyl synanthrin of 2.0g is taken to be dissolved in
In 50.0mLDMSO solution, 0.1gCuI is sequentially added, 0.5mL triethylamine solutions, then slowly drop 10.0g is folded in (2) plus stating
Nitrogen diphenyl phosphate solution, under nitrogen protection, 75 DEG C of reaction 48h.After reaction, above-mentioned reaction solution is poured into acetone soln
In, Precipitation is filtered, is repeatedly washed with acetone, sample dialysis freeze-drying.
Embodiment 2：
(1) preparation of alkynyl synanthrin：It takes the synanthrin of 1.6g to be scattered in 30mL isopropanols to stir evenly, addition
The propargyl bromide solution of 3.0mL is added dropwise after activating 1h in 25.0mL5.0%NaOH solution, and 60 DEG C of the reaction was continued 4h, reaction terminates,
It pours into ethanol solution, Precipitation, filters, after being washed repeatedly with ethyl alcohol, sample freeze-drying；
(2) preparation of diphenyl phosphate azide：It takes 1.5mL diphenyl phosphate chlorides in round-bottomed flask, 2.0g nitrine is added
Change sodium, the acetone soln of 30.0mL is then added, react at room temperature 5h, vacuum distillation removes solvent；
(3) preparation of 1,2,3- triazoles diphenyl phosphate synanthrin derivative：The above-mentioned alkynyl synanthrin of 2.0g is taken to be dissolved in
In 50.0mLDMSO solution, 0.13gCuI is sequentially added, 1.0mL triethylamine solutions, then slow drop 12.0g, which is added, states in (2)
Diphenyl phosphate azide solution, under nitrogen protection, 75 DEG C of reaction 48h.After reaction, above-mentioned reaction solution is poured into acetone soln
In, Precipitation is filtered, is repeatedly washed with acetone, sample dialysis freeze-drying.
Embodiment 3：
(1) preparation of alkynyl synanthrin：It takes the synanthrin of 1.6g to be scattered in 50mL isopropanols to stir evenly, addition
The propargyl bromide solution of 4.0mL is added dropwise after activating 1h in 34.0mL5.0%NaOH solution, and 60 DEG C of the reaction was continued 5h, reaction terminates,
It pours into ethanol solution, Precipitation, filters, after being washed repeatedly with ethyl alcohol, sample freeze-drying；
(2) preparation of diphenyl phosphate azide：It takes 1.5mL diphenyl phosphate chlorides in round-bottomed flask, 2.2g nitrine is added
Change sodium, the acetone soln of 35.0mL is then added, react at room temperature 5h, vacuum distillation removes solvent；
(3) preparation of 1,2,3- triazoles diphenyl phosphate synanthrin derivative：The above-mentioned alkynyl synanthrin of 2.0g is taken to be dissolved in
In 50.0mLDMSO solution, 0.15gCuI is sequentially added, 1.5mL triethylamine solutions, then slow drop 14.0g, which is added, states in (2)
Diphenyl phosphate azide solution, under nitrogen protection, 75 DEG C of reaction 48h.After reaction, above-mentioned reaction solution is poured into acetone soln
In, Precipitation is filtered, is repeatedly washed with acetone, sample dialysis freeze-drying.
Embodiment 4：
(1) preparation of alkynyl synanthrin：It takes the synanthrin of 1.6g to be scattered in 60mL isopropanols to stir evenly, addition
The propargyl bromide solution of 6.3mL is added dropwise after activating 1h in 50.0mL5.0%NaOH solution, and 60 DEG C of the reaction was continued 5h, reaction terminates,
It pours into ethanol solution, Precipitation, filters, after being washed repeatedly with ethyl alcohol, sample freeze-drying；
(2) preparation of diphenyl phosphate azide：It takes 1.5mL diphenyl phosphate chlorides in round-bottomed flask, 2.7g nitrine is added
Change sodium, the acetone soln of 50.0mL is then added, react at room temperature 5h, vacuum distillation removes solvent；
(3) preparation of 1,2,3- triazoles diphenyl phosphate synanthrin derivative：The above-mentioned alkynyl synanthrin of 2.0g is taken to be dissolved in
In 50.0mLDMSO solution, 0.2gCuI is sequentially added, 2.0mL triethylamine solutions, then slowly drop 15.0g is folded in (2) plus stating
Nitrogen diphenyl phosphate solution, under nitrogen protection, 75 DEG C of reaction 48h.After reaction, above-mentioned reaction solution is poured into acetone soln
In, Precipitation is filtered, is repeatedly washed with acetone, sample dialysis freeze-drying.
Fig. 1 is the infrared spectrogram of synanthrin, and Fig. 2 is the infrared spectrogram of alkynyl synanthrin prepared by the embodiment of the present invention 3, from
2118cm known to Fig. 2-1For the absorption peak of C ≡ C, it was demonstrated that the successful synthesis of alkynyl synanthrin.
Fig. 3 is the infrared spectrum of diphenyl phosphate azide prepared by the embodiment of the present invention 3, as can be seen from Figure 3 2171cm-1It is folded
The absorption peak of nitrogen, it was demonstrated that the successful synthesis of diphenyl phosphate azide.
Fig. 4 is the infrared spectrogram of 1,2,3- triazole diphenyl phosphate synanthrin derivatives prepared by the embodiment of the present invention 3,
Compared with Fig. 3,2118cm in Fig. 4-1Locate alkynyl peak to disappear, while 1612,1489,778cm-1The peak that place occurs is 1,2,
The absorption peak of 3- triazoles and phenyl ring, 1207cm-1The peak that place occurs is the absorption peak of P=O, it was demonstrated that 1,2,3- triazole di(2-ethylhexyl)phosphate
The successful synthesis of phenyl ester synanthrin derivative.
Fig. 5 is that 1,2,3- triazole diphenyl phosphate synanthrin derivatives remove DPPH free radicals in the embodiment of the present invention 3
Ability, CPI 1,2,3- triazole diphenyl phosphate synanthrin derivatives.
Fig. 6 is that 1,2,3- triazole diphenyl phosphate synanthrin derivatives remove hydroxyl radical free radical in the embodiment of the present invention 3
Ability, CPI 1,2,3- triazole diphenyl phosphate synanthrin derivatives.
Fig. 7 is that 1,2,3- triazole diphenyl phosphate synanthrin derivatives remove superoxide anion certainly in the embodiment of the present invention 3
By the ability of base, CPI 1,2,3- triazole diphenyl phosphate synanthrin derivatives.
The test of oxidation resistance：Vc (positive control), synanthrin and 1,2,3- triazole diphenyl phosphate chrysanthemums are measured respectively
Sugar derivatives is respectively to hydroxyl radical free radical, the Scavenging activity of ultra-oxygen anion free radical and DPPH free radicals.Fig. 5 is embodiment 3
In 1,2,3- triazole diphenyl phosphate synanthrin derivatives remove DPPH free radicals ability, Fig. 6 be embodiment 3 in 1,2,3- tri-
Nitrogen azoles diphenyl phosphate synanthrin derivative removes the ability of hydroxyl radical free radical, and Fig. 7 is 1,2,3- triazole di(2-ethylhexyl)phosphates in embodiment 3
Phenyl ester synanthrin derivative removes the ability of ultra-oxygen anion free radical.As shown, in the active testing for removing DPPH free radicals
In, when sample concentration is 1.6mg/mL, synanthrin has 25.9% clearance rate, however 1,2,3- triazole diphenyl phosphate synanthrin
Derivative removes DPPH abilities and is increased to 51.0%.During removing the active testing of hydroxyl radical free radical, 1,2,3- triazole
Diphenyl phosphate synanthrin derivative can almost remove hydroxyl radical free radical in 1.6mg/mL sample concentrations, relative to synanthrin
20.6% clearance rate, 1,2,3- triazole diphenyl phosphate synanthrin derivative is notable to the scavenging effect of hydroxyl radical free radical
's.Meanwhile remove superoxide radical active testing during, synanthrin to superoxide anion almost without Scavenging activity, but
It is that the clearance rates of 1,2,3- triazole diphenyl phosphate synanthrin derivatives almost maintains an equal level with Vc, even if the sample in 0.1mg/mL is dense
Under degree, 92.0% is reached to the clearance rate of ultra-oxygen anion free radical.In conclusion 1,2,3- triazole diphenyl phosphate chrysanthemum
Sugar derivatives significantly improves the antioxidant activity of synanthrin, can be further applicable to the fields such as food medical treatment cosmetics.
Claims (6)
1. one kind 1,2,3- triazole diphenyl phosphate synanthrin derivatives, it is characterised in that：The 1,2,3- triazoles di(2-ethylhexyl)phosphate
Phenyl ester synanthrin derivant structure formula is as follows：
The synanthrin derivative molecular amount is 10,000 or so.
2. according to claim 11,2,3- triazole diphenyl phosphate synanthrin derivatives, it is characterised in that：Described 1,2,
3- triazole diphenyl phosphate synanthrin derivatives can be applied to the anti-oxidant aspect in food medical cosmetic field.
3. the preparation method of as described in claim 11,2,3- triazole diphenyl phosphate synanthrin derivatives, it is characterised in that：
Using synanthrin as raw material, alkynyl synanthrin is made using propargyl bromide, Azide is carried out using sodium azide with diphenyl phosphate chloride, is led to
Click reactions are crossed, 1,2,3- triazole diphenyl phosphate synanthrin derivatives are made, include the following steps：
(1) preparation of alkynyl synanthrin：It takes a certain amount of synanthrin to be scattered in isopropanol to stir evenly, is added a certain amount of 5.0%
A certain amount of propargyl bromide solution is added dropwise after activating 1h in NaOH solution, and 60 DEG C of the reaction was continued 4h, reaction terminates, and it is molten to pour into ethyl alcohol
In liquid, Precipitation filters, after being washed repeatedly with ethyl alcohol, sample freeze-drying；
(2) preparation of diphenyl phosphate azide：It takes a certain amount of diphenyl phosphate chloride in round-bottomed flask, is added a certain amount of folded
Then sodium nitride is added a certain amount of acetone soln and makees solvent, react at room temperature 5h, and vacuum distillation removes solvent；
(3) preparation of 1,2,3- triazoles diphenyl phosphate synanthrin derivative：A certain amount of above-mentioned alkynyl synanthrin is taken to be dissolved in centainly
In the DMSO solution of amount, a certain amount of CuI is sequentially added, then triethylamine solution is slowly added dropwise described in a certain amount of (2)
Diphenyl phosphate azide solution, under nitrogen protection, above-mentioned reaction solution is poured into acetone soln by 75 DEG C of reaction 48h after reaction
In, Precipitation is filtered, is repeatedly washed with acetone, sample dialysis freeze-drying.
4. the preparation method of according to claim 31,2,3- triazole diphenyl phosphate synanthrin derivatives, feature exist
In：Step (1) synanthrin, isopropanol, 5.0%NaOH solution, propargyl bromide dosage are respectively：Per 1.6g synanthrin, 20.0-
60.0mL isopropanols, 25.0-50.0mL5.0%NaOH solution, 2.4-6.3mL propargyl bromides.
5. the preparation method of according to claim 31,2,3- triazole diphenyl phosphate synanthrin derivatives, feature exist
In：Step (2) diphenyl phosphate chloride, sodium azide, acetone dosage are respectively：Per 1.5mL diphenyl phosphate chlorides, 1.4-
2.7g sodium azide, 25.0-50.0mL acetone.
6. the preparation method of according to claim 31,2,3- triazole phenyl phosphate synanthrin derivatives, it is characterised in that：
Step (3) the alkynyl synanthrin, DMSO, CuI, triethylamine, diphenyl phosphate azide solution usage are respectively：Per 2.0g alkynyl chrysanthemums
Sugar, 50.0mLDMSO, 0.1-0.2gCuI, 0.5-2.0mL triethylamines, 10.0-15.0g diphenyl phosphate azide solution.
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Application publication date: 20181019 |